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Preheat oven to 425 degrees Fahrenheit and line a baking sheet with parchment paper for easy cleanup. Carefully halve the pumpkin and scoop out the seeds (you can roast the seeds if you’d like—see note—but you won’t need them for this recipe).
Slice each pumpkin halve in half to make quarters. Brush or rub 1 tablespoon olive oil over the flesh of the pumpkin and place the quarters, cut sides down, onto the baking sheet. Roast for 35 minutes or longer, until the orange flesh is easily pierced through with a fork. Set it aside to cool for a few minutes.
Heat the remaining 3 tablespoons olive oil in a large Dutch oven or heavy-bottomed pot over medium heat. Once the oil is shimmering, add onion, garlic and salt to the skillet. Stir to combine. Cook, stirring occasionally, until onion is translucent, about 8 to 10 minutes. In the meantime, peel the pumpkin skin off the pumpkins and discard the skin.
Add the pumpkin flesh, cinnamon, nutmeg, cloves, cayenne pepper (if using), and a few twists of freshly ground black pepper. Use your stirring spoon to break up the pumpkin a bit. Pour in the broth. Bring the mixture to a boil, then reduce heat and simmer for about 15 minutes, to give the flavors time to meld.
While the soup is cooking, toast the pepitas in a medium skillet over medium-low heat, stirring frequently, until fragrant, golden and making little popping noises. You want them to be nice and toasty, but not burnt. Transfer pepitas to a bowl to cool.
Once the pumpkin mixture is done cooking, stir in the coconut milk and maple syrup. Remove the soup from heat and let it cool slightly. You can use an immersion blender to blend this soup in the pot. I prefer to use my stand blender, which yields the creamiest results—working in batches, transfer the contents of the pan to a blender (do not fill your blender past the maximum fill line!). Securely fasten the blender’s lid and use a kitchen towel to protect your hand from steam escaping from the top of the blender as you purée the mixture until smooth. Transfer the puréed soup to a serving bowl and repeat with the remaining batches.
Taste and adjust if necessary (I thought the soup was just right as is, but you might want to add more coconut milk for extra creaminess/milder flavor, or maple syrup to make it a little sweeter).
Ladle the soup into individual bowls. Sprinkle pepitas over the soup and serve. Let leftover soup cool completely before transferring it to a proper storage container and refrigerating it for up to 4 days (leftovers taste even better the next day!). Or, freeze this soup for up to 3 months.